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10 Outfits I Was Obsessed With This Month (And Exactly Where to Get Them)

10 Outfits I Was Obsessed With This Month (And Exactly Where to Get Them)

From date nights to sports mom duty...

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Molly Sims
May 11, 2025
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10 Outfits I Was Obsessed With This Month (And Exactly Where to Get Them)
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January and February felt like they dragged on forever, but everything since has been a total blur. April was one of the craziest months—I went to Cabo twice, hit up Chump-Con in Vegas, moved, and so much more. Needless to say, I’ve been all over the place—which means I’ve worn a little bit of everything: poolside looks, nighttime outfits, casual go-tos.

So I thought it’d be fun to round up my top 10 favorite fits from April.

I’m linking everything that’s still in stock—and of course, adding some similar dupes and alternatives for anything that’s sold out.

This one’s jam-packed, so let’s get right into it.


1. This Denim on Denim Fit

I think it’s safe to say I’m in my denim era.

I wore this look to the office and went straight out for drinks after. It’s a matching set from Jenni Kayne, and I’m obsessed. The top is your classic denim button up shirt, that fits a little oversized, and the pants are wide leg fit with a super flattering pleat. This set is not only totally chic, but also so comfortable and practical.

For accesories I added my Khaite Robbi belt, which is sold out everywhere, so this Toteme one gives the same vibe. And for shoes I wore my Chanel denim flats (also sold out, sorry) but this Margaux pair is such a good dupe, that I actually also own.

As for jewelry, I wore my Adina Reyter heart necklace, Kendra Scott hoops, Adina Reyter diamond huggies, my little diamond trio studs, Anita Ko gold cuff, and my diamond ear cuff.

OUTFIT DETAILS

2. I’m Calling it the Chic Mom Cocktail Look

Loved this look because even though it was technically during the day (hello, it’s Vegas), I went all out. I wore this to Chump Con and seriously had the best time, while also looking chic as heck. You could totally wear this out to drinks, a date night, or a cocktail hour.

I Kept it casual on top with a simple TWP tee but made it a little party on the bottom with this sequin TWP skirt. Felt so effortless but still glam which was SO fun.

For accessories, I kept it fairly simply since the skirt really is the star of the show and I just paired it with my white Alevi Milano pumps (which I love), but I found a similar pair from Retrofête that's slingback and more affordable. For the bag, I carried my white Jimmy Choo clutch with gold hardware.

OUTFIT DETAILS

3. The Polka Dot Moment

This is basically my go-to work uniform — I always want to look cute but still comfortable and practical. A midi skirt and sweater combo truly is the perfect pairing.

My black cashmere turtle neck is from Jenni Kayne and my flowy polka dot maxi skirt if from Wardrobe NYC. It actually has a matching top too, which I also own and wore to the Kelly Clarkson show. It’s the perfect example of how you can seriously get so many uses our of a matching set.

For accessories, I wore my black mesh Chanel ballet flats, which I sadly can’t find online, but I did find a similar pair from Loro Piana that are so classy and chic, and my sunnies are, of course, my tried and true Celines.

OUTFIT DETAILS

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